Bis(2-hydroxy-1-naphthyl) disulfide

Base Information

• Chemical Name: Bis(2-hydroxy-1-naphthyl) disulfide
• CAS No.: 42521-82-4
• Molecular Formula: C20H14O2S2
• Molecular Weight: 350.462
• Hs Code.: 2930909090
• European Community (EC) Number: 631-003-0
• UNII: 3XFG6MQ9G2
• DSSTox Substance ID: DTXSID70195311
• Nikkaji Number: J3.202.883G
• Wikidata: Q27078087
• Pharos Ligand ID: 76UUJPH5JQKQ
• ChEMBL ID: CHEMBL472940
• Mol file: 42521-82-4.mol

Synonyms:IPA-3;42521-82-4;IPA 3;Bis(2-hydroxy-1-naphthyl) disulfide;1,1'-Dithiodi-2-naphthol;1,1'-disulfanediylbis(naphthalen-2-ol);IPA3;2-Naphthol, 1,1'-dithiodi-;2-Naphthalenol, 1,1'-dithiobis-;1-[(2-hydroxynaphthalen-1-yl)disulfanyl]naphthalen-2-ol;UNII-3XFG6MQ9G2;3XFG6MQ9G2;CHEMBL472940;1,1'-Dithiodi-2-naphthtol;1,1'-disulfanediyldinaphthalen-2-ol;dihydroxydinaphthyldisulphide;MLS006011676;F0400-0044;GTPL8940;SCHEMBL4907161;CHEBI:95062;DTXSID70195311;CHEBI:101355;HMS3229J05;HMS3263P06;HMS3414C17;HMS3653G03;HMS3678C17;Tox21_501272;BDBM50112354;MFCD00388917;s7093;AKOS001589606;CCG-222576;CS-1432;LP01272;SDCCGSBI-0207173.P002;1,1'-disulfanediyldi(naphthalen-2-ol);IPA-3, >=95% (HPLC), powder;NCGC00186047-01;NCGC00186047-02;NCGC00186047-12;NCGC00261957-01;AS-82043;HY-15663;SMR001456562;SW220299-1;D83674;1-[(2-hydroxy-1-naphthyl)disulfanyl]-2-naphthol;A918483;1-(2-hydroxynaphthalen-1-yl)disulfanylnaphthalen-2-ol;Q27078087;Z57109489;1081767-20-5

Chemical Property of Bis(2-hydroxy-1-naphthyl) disulfide

Chemical Property:

• Boiling Point: 543.7±35.0 °C(Predicted)
• PKA: 7.52±0.50(Predicted)
• PSA: 91.06000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: 6.20360
• Storage Temp.: Store at +4°C
• Sensitive.: Light Sensitive
• Solubility.: DMSO: >20mg/mL
• Water Solubility.: Soluble in DMSO or ethanol. Insoluble in water.
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 350.04352203
• Heavy Atom Count: 24
• Complexity: 380

Purity/Quality:

98%,99%, ^*data from raw suppliers

IPA 3 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 41-50/53
• Safety Statements: 26-39-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=C2SSC3=C(C=CC4=CC=CC=C43)O)O
• Description: IPA-3 (42521-82-4) is a selective allosteric inhibitor of Group 1 p21-activated kinase (PAK1 IC50?= 2.5 μM)1?via covalent binding to the PAK1 regulatory domain preventing binding to the upstream activator Cdc422. IPA-3 has been shown to induce cell death in human leukemic cell lines3, significantly inhibit TGFβ1-induced prostate cell epithelial to mesenchymal transition4?and inhibit the growth of liver cancer cells5.
• Uses: p21-activated kinase 1 (PAK1) is a member of a family non-receptor serine/threonine kinases that are vital to normal cell function. Binding of various upstream partners to PAK1 results in release of an autoinhibitory domain that blocks activity of the kinase domain. PAK1 expression and activity is upregulated in several human cancers and is a potential therapeutic target for cancer intervention. IPA-3 is a cell-permeable allosteric inhibitor of PAK1 that is non-competitive with respect to ATP binding (IC50 = 2.5 μM). It does not, however, inhibit the activity of PAK1 that has been pre-activated with Cdc42. IPA-3 binds covalently to the PAK1 regulatory domain (apparent Kd = 1.9 uM) and prevents binding to the upstream activator Cdc42.[Cayman Chemical] Acts as an allosteric inhibitor of Pak1

Technology Process of Bis(2-hydroxy-1-naphthyl) disulfide

There total 4 articles about Bis(2-hydroxy-1-naphthyl) disulfide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

β-naphthol (135-19-3) → 1,1'-thiobis(2-naphthol) (17096-15-0) + bis-(2-hydroxy-1-naphthyl)disulphide (42521-82-4)

Guidance literature:

With sodium hydroxide; sulfur;

DOI:10.1111/j.1365-2621.2002.tb09451.x DOI:10.1111/j.1365-2621.2002.tb09459.x

Reference yield:

furan-2,3,5(4H)-trione pyridine (1:1) + β-naphthol (135-19-3) → 1,1'-thiobis(2-naphthol) (17096-15-0) + bis-(2-hydroxy-1-naphthyl)disulphide (42521-82-4)

Guidance literature:

DOI:10.1111/j.1365-2621.2002.tb09451.x DOI:10.1111/j.1365-2621.2002.tb09459.x

Reference yield:

methanol (67-56-1) + naphth<1,2-d>-1,3-oxathiol-2-one (22791-05-5) → 1,1'-thiobis(2-naphthol) (17096-15-0) + bis-(2-hydroxy-1-naphthyl)disulphide (42521-82-4)

Guidance literature:

upstream raw materials:

β-naphthol

methanol

naphth<1,2-d>-1,3-oxathiol-2-one

chloroform

Downstream raw materials:

1,1'-thiobis(2-naphthol)

1,1'-bi-2-naphthol

2-acetoxy-1-picrylmercapto-naphthalene

2-methoxy-1-picrylmercapto-naphthalene